This episode is brought to you by SoulSway - use code LAMN50 for 50% off your new favorite workout. In this powerful episode of Look At Me Now, Alexis sits down with survivor, storyteller, and author Cleo Young for a raw, unflinching conversation about life in — and beyond — the cycle of incarceration. From a childhood shaped by instability to decades spent navigating state and federal prison systems, Cleo shares the pivotal moments that pushed him toward change, the lessons he learned in the most unlikely places, and how he ultimately found freedom on the open road as a long-haul trucker. 00:00 – A somber opening: Alexis meets Cleo 00:41 – “Survivor scholar of life”: A different kind of introduction 02:03 – The poem that made a psychologist cry 04:03 – “The gangster”: A lyrical truth from inside the system 05:09 – Ten years for survival: Life in the SHU 06:39 – Forgiving everyone — including himself 08:51 – Coming home, going back: Why change is so hard 10:10 – Pride, provision, and the pull of the streets 11:21 – From tiptoeing to knee-deep in the game 12:34 – Breaking into school for a VCR: Early survival tactics 13:28 – Boys Ranch revelations: Poverty has many faces 15:26 – Team-building, manners, and what the hood can’t teach you 16:21 – Thriving in structure, drowning in chaos 17:43 – Running away, returning home 18:51 – Knowing right from wrong, but feeling out of options 20:29 – The urgency of survival in the ’90s 21:02 – An aunt’s lifeline and a high school graduation 22:44 – Gangs as family and safety net 23:00 – First prison sentence at 18: A family reunion behind bars 24:33 – Denied the chance to learn a trade 26:11 – Smuggling runs with his mother 27:02 – Telemarketing, renovation, and a glimpse at stability 29:22 – The job he loved — and the parole violation that ended it 31:49 – Starting over again and again 34:09 – General Relief and the temptation next door 35:45 – Selling drugs — and the raid that changed everything 37:33 – It’s not about knowing right from wrong 39:37 – Growing up without choice or autonomy 40:47 – The urgency that erases patience 41:46 – Losing friends to drugs, violence, and prison 42:09 – Why this incarceration felt different 43:27 – Filling time with jobs and hustles 44:49 – Thinking he could “beat the system” — and losing again 45:57 – Federal time: 20 years for marijuana 47:20 – Fighting his case from the law library 48:51 – Learning from unexpected mentors in prison 49:49 – Winning an appeal and walking free 50:26 – Cancer, loss, and the system of “Why?” 53:04 – Radical self-accountability 54:24 – Early release, hard lessons, and leaving gang life behind 56:23 – Choosing trucking: Covid-proof, recession-proof, felony-friendly 58:00 – Starting from zero and loving life without fences 59:49 – From hopelessness to hope: What he tells others 01:01:06 – Know where you’re going — and do the research 01:02:18 – Choosing the high road when the low road calls 01:03:05 – Surviving the minute, the hour, the day 01:05:10 – The pride barrier: Why asking for help is so hard 01:07:21 – Being present and recognizing your worth 01:09:09 – Freedom, beauty, and the power of possibility 01:10:04 – Writing books and living fully 01:12:21 – Making the most of every moment 01:13:21 – “You’re worth it and you deserve it” 01:14:09 – First podcast appearance — and where to find Cleo Connect with Cleo: Book: How to Start an LLC by Olivia J. Young Instagram: @cleo_young (if applicable) Follow Alexis @alexis_artin Learn more at AlexisArtin.com Save 50% on any SoulSway experience with code LAMN50 This is an Operation Podcast production
